Hydrochloric Acid → HCID 19085484, compound

HRID 962448Notes

Reaction equation

HRID 962448 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH:4]=[C:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH2:6]1.C(=O)(O)[O-].[Na+].[ClH:26]>[Pd].CCOCC>[ClH:26].[ClH:26].[CH3:20][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 19085409HCID 19085409, compound

Product 1

HCID 19085484HCID 19085484, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 4-(2-dimethylaminoethylidene)-1-(2-phenoxyethyl)piperidine (2.0 g) (The product of Example 37 was treated with aqueous sodium bicarbonate solution and ether. The ether was separated, washed, dried and evaporated to give the free base.) in IMS (200 ml) and a catalytic amount of 10% palladium on charcoal was hydrogenated at atmospheric pressure for 5 hours. The catalyst was removed by filtration. The filtrate was evaporated to give an oil which was dissolved in ether and then acidified with ethereal hydrogen chloride. The precipitate was collected by filtration and recrystallised from IMS to give 4-(2-dimethylamino-ethyl)-1-(2-phenoxyethyl)piperidine dihydrochloride, m.p. 286°-288° C.

Workup

  1. customThe ether was separated
  2. washwashed
  3. customdried
  4. customevaporated
  5. customto give the free base
  6. customThe catalyst was removed by filtration
  7. customThe filtrate was evaporated
  8. customto give an oil which
  9. filtrationThe precipitate was collected by filtration
  10. customrecrystallised from IMS

Sources & evidence

ORD record
ord-af36412072f84598959a12b29558727c
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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